EP0636121A1 - Arthropodicidal pyrazole sulfonates - Google Patents

Arthropodicidal pyrazole sulfonates

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Publication number
EP0636121A1
EP0636121A1 EP93905036A EP93905036A EP0636121A1 EP 0636121 A1 EP0636121 A1 EP 0636121A1 EP 93905036 A EP93905036 A EP 93905036A EP 93905036 A EP93905036 A EP 93905036A EP 0636121 A1 EP0636121 A1 EP 0636121A1
Authority
EP
European Patent Office
Prior art keywords
group
alkyl
haloalkyl
compounds
optionally substituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP93905036A
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German (de)
English (en)
French (fr)
Inventor
Bruce Lawrence Finkelstein
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Dunlena Pty Ltd
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Dunlena Pty Ltd
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Filing date
Publication date
Application filed by Dunlena Pty Ltd filed Critical Dunlena Pty Ltd
Publication of EP0636121A1 publication Critical patent/EP0636121A1/en
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
    • C07D231/52—Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/28—Two oxygen or sulfur atoms
    • C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
    • C07D231/32—Oxygen atoms
    • C07D231/34—Oxygen atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached in position 4

Definitions

  • U.S. Patent 3,966,574 discloses insecticidal sulfonates that contain a heteroaromatic ring having three heteroatoms.
  • U.S. Patent 4,791,127 discloses insecticidal thiazole sulfonates and Jacobsen, et al., Pest. Sci., (1990), 29, 96-100 discloses insecticidal oxazole sulfonates.
  • Arthropodicidal pyrazole sulfonates of Formula I have hitherto been unknown.
  • This invention pertains to compounds of Formula I, including all geometric and stereoisomers, agriculturally suitable salts thereof, agricultural compositions containing them and their use for the control of arthropods and nematodes in both agronomic and nonagronomic environments.
  • the compounds are
  • R 1 is selected from the group C1-C3 alkyl and C1-C3 haloalkyl;
  • R 2 is selected from the group C j -Cg alkyl, C3-C6 cycloalkyl, C 2 -C 0 - alkenyl and C 2 -Cg alkynyl each of which can be optionally substituted with R 5 ; or R 2 is selected from the group Cj-Cg haloalkyl, N(R 7 )R 8 , C 3 -C 6 cyclohaloalkyl, C2-C 6 haloalkenyl, C2-C 6 haloalkynyl, C4-C7 cycloalkylalkyl and C4-C7 cycloalkylalkyl substituted with R 6 ;
  • R 3 and R 4 are independently selected from the group H, Cr-Cg haloalkyl, C r C 6 alkoxy, C r C 6 haloalkoxy, C ⁇ -C 6 alkylthio, Cj-Cg hdoalkylthio, C3-C6 cyclohaloalkyl, C ⁇ -Cg haloalkenyl, C 2 -Cg haloalkynyl, C4-C7 cycloa-kylalkyl, C j -C ⁇ alkylsulfmyl, C j -Cg hdoalkykulf-nyl, Ci-Cg -tlkylsulfonyl, C ⁇ C ---alo-dkylsulfonyl,
  • R 5 and R 13 are independently selected from the group CN, SCN, NO 2 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , OC(O)R 9 , OSO 2 R 9 , Si(R 9 )(R 10 )(R n ), CO 2 R 9 , C(O)N(R 9 )R 10 , C(O)R 9 , N(R 9 )R 10 andphenyl optionally substituted with R 12 ;
  • R 6 is selected from the group halogen, CN and Ci -C 2 alkyl
  • ⁇ R 7 is selected from the group Cj-Cg alkyl optionally substituted with R 16 , C3-C6 cycloalkyl optionally substituted with R 19 , and C4-C7 cycloalkylalkyl optionally substituted with R 19 ;
  • R 8 is selected from the group H, CN, Ci -Cg haloalkyl and Cj-Cg a ⁇ £ l optionally substituted with CN;
  • R 7 and R 8 can be taken together to form -(CH 2 ) 2 -, -(CH 2 ) 3 -, -(CH 2 ) 4 -, -(CH 2 ) 5 - or -CH 2 CH 2 -O-CH 2 CH 2 -;
  • R 9 , R 10 and R 11 are independently selected from the group C1-C3 alkyl and C 1 -C3 haloalkyl; R 12 and W are independently selected from the group halogen, C ⁇ -C 2 alkyl,
  • R 14 and R 15 are independently selected from the group H, C j -Cg alkyl, C j -Cg haloalkyl, C 2 -Cg alkylcarbonyl, C 2 -C6 alkoxycarbonyl, C j -Cg alkylsulfonyl and C(O)N(Rl 7 )R* 8 ; or
  • R 14 and R 15 can be taken together to form -(CH 2 ) 2 -, -(CH 2 ) 3 -, -(CH ⁇ -, -(CH2) 5 - or -CH 2 CH 2 -O-CH 2 CH 2 -; -
  • R 16 is selected from the group 1 to 5 halogens, CN, C ⁇ -C 2 alkoxy, C j - ⁇ alkylthio, C r C 2 alkylsulfonyl and C 3 -C 6 trialkylsilyl;
  • R 17 and R 18 are independently selected from the group H and C j -C3 alkyl; and R 19 is selected from the group 1 to 5 halogens, C1-C3 alkyl, CN, C j -C 2 alkoxy, C ⁇ -C 2 alkylthio, C ⁇ -C alkylsulfonyl and C3-C6 trialkylsilyl.
  • R 3 and R 4 are independently selected from the group H, C j -C 2 alkyl, C r C 2 haloalkyl, C r C 2 alkoxy, N(R 1 )R!5 and halogen; and R 14 andR 15 are independently selected from the group H and C r C 6 alkyl.
  • Preferred Compounds B are compounds of Preferred A wherein Q is Q-l.
  • Preferred Compounds C are compounds of Preferred A wherein Q is Q-2.
  • Preferred Compounds D are compounds of Preferred A wherein Q is Q-3.
  • stereoisomers Some of the compounds of this invention can exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers and geometric isomers.
  • the present invention comprises mixtures, individual stereoisomers, and optically active mixtures of compounds of Formula I as well as agriculturally suitable salts thereof.
  • alkyl used either alone or in compound word such as "haloalkyl”, denotes straight or branched alkyl such as methyl, ethyl, n-propyl, isopropyl, or the different butyl, pentyl or hexyl isomers.
  • Alkoxy denotes methoxy and ethoxy.
  • Alkenyl denotes straight or branched chain alkenes such as vinyl, 1-propenyl, 2-propenyl and the different butenyl, pentenyl and hexenyl isomers.
  • Cycloalkylalkyl denotes cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl attached to a straight or branched C1-C4 alkylene group.
  • the ter “trialkylsilyl” denotes silicon with three alkyl substituents.
  • the term "Alkoxy” denotes methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.
  • alkylsulfonyl denotes CH 3 S(O) 2 , CH 3 CH 2 S(O) 2 , CH 3 CH 2 CH 2 S(O) 2 , (CH 3 ) 2 CHS(O) 2 and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers.
  • alkylsulf ⁇ nyl denotes CH 3 S(O) and CH 3 CH 2 S(O).
  • halogen either alone or in compound words such as “haloalkyl”, denotes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl” said alkyl may be partially or fully substituted with halogen atoms, which may be the same or different. Examples of haloalkyl include CH 2 CH 2 F, CF 2 CF 3 and CH 2 CHFC1. The teims "haloalkenyl” and “haloalkynyr' are defined analogously to the term “haloalkyl".
  • C j -Cj The total number of carbon atoms in a substituent group is indicated by the "C j -Cj" prefix where i and j are numbers from 1 to 7.
  • C 2 alkoxycarbonyl designates C(O)OCH3
  • C3 alkoxycarbonyl designates C(O)OCH 2 CH 3 .
  • Equation 2 The synthesis of the compounds 3 is known. Equation 2
  • the hydroxy pyrazoles 1 wherei--- Q is Q-2 can be prepared from alkoxy compounds 4 by treatment with iodotrimethylsilane or aqueous acid such as hydrobromic acid in acetic acid as shown in Equation 3. Equation 3
  • the compounds of Formula 4 can be prepared by treatment of an alkoxypyrazole 5 with the appropriate acid chloride, sulfonyl chloride, sulfinylchloride or sulfenyl chloride (6) and base as shown in Equation 4.
  • a thiation reagent such as P 2 S 5 or 2,4-b--s(4-memoxyphenyl)-l,3-dit----a-2,4-diphosphet-me-2,4-disulfide.
  • the synthesis of 4-alkoxypyrazoles is known to one skilled in the art. (For instance see:
  • the hydroxy pyrazoles 1 wherein Q is Q-3 can be prepared by cyclization of ⁇ -oxohydrazides (7) with a base such as sodium ethoxide in a solvent such as ethanol as shown in Equation 5.
  • the compounds of Formula 7 are prepared by known methods. Equation 5
  • compounds of Formula I wherein Q is Q-l or Q-3 can be prepared by reaction of a pyrazole sulfonate 8 with a compound of Formula 6 and base as shown in Equation 6.
  • the ratio of products obtained will depend on the nature of the R 3 and R 4 groups. In some instances, only one product will be obtained.
  • the compounds of Formula 8 can be prepared by the reaction of a hydroxypyrazole 9 with a sulfonyl halide and base as showff n Equation 7.
  • the synthesis of compounds of Formula 9 is known. - ⁇
  • compounds of Formula I wherein Q is Q-2 can be prepared from pyrazole sulfonates of Formula 10 which in turn can be prepared from hydroxy pyrazoles of Formula II as shown in Equation 8. Equation 8
  • Compounds of this invention will generally be used in formulation with an agriculturally suitable carrier comprising a liquid or solid diluent or an organic solvent.
  • Useful formulations include dusts, granules, baits, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates, dry flowables and the like, consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.
  • Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation.
  • the formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up 100 weight percent.
  • Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents and solvents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, etc.
  • Fine solid compositions are made by blending and, usually, grinding as in a hammer mill or fluid energy mill- Water-dispersible granules can be produced by agglomerating a fine powder composition; see for example, Cross et al., Pesticide Formulations, W-ishington, D.C., 1988, pp 251-259.
  • Suspensions are prepared by wet-milling; see, for example, U.S.3,060,084.
  • Granules and pellets can be made by spraying the active material upon preformed granular carriers or by agglomeration techniques.
  • Pellets can be prepared as described in U.S.4,172,714. Water-dispersible and water-soluble granules can also be prepared as taught in DE ⁇ 3 ,246,493.
  • Compound 1 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium hgi-irisulfonate 4.0% sodium siHcoaluminate 6.0% montmor-llonite (calcined) 23.0%.
  • Example C Extruded Pellet Compound 1 25.0% anhydrous sodium sulfate 10.0% crude calcium Ugninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium magnesium bentonite 59.0%.
  • Example D Extruded Pellet Compound 1 25.0% anhydrous sodium sulfate 10.0% crude calcium Ugninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium magnesium bentonite 59.0%.
  • Example D Extruded Pellet Compound 1 25.0% anhydrous sodium sulfate 10.0% crude calcium Ugninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium magnesium bentonite 59.0%.
  • Compound 1 20.0% blend of oil soluble sulfonates and polyoxyethylene ethers 10.0% isophorone 70.0%.
  • the compounds of this invention exhibit activity against a wide spectrum of foliar-feeding, fruit-feeding, seed-feeding, aquatic and soil-inhabiting arthropods (term “arthropod” includes insects, mites and nematodes) which are pests of growing and stored agronomic crops, forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, and public and animal health. Those skilled in the art will appreciate that not all compounds are equally effective against all pests.
  • all of the compounds of this invention display activity against pests that include: eggs, larvae and adults of the Order Lepidoptera; eggs, foliar-feeding, fruit-feeding, root-feeding, seed-feeding larvae and adults of the Order Coleoptera; eggs, immatures and adults of the
  • the compounds of this invention are also active against pests of the Orders Hymenoptera, Isoptera, Phthiraptera, Siphonoptera, Blattaria, Thysanaura and Pscoptera; pests belonging to the Class Arachnida and Phylum Platyhelminthes.
  • the compounds are particularly active against southern cornjrootworm iabrotica undecimpunctata howard ⁇ ), aster leafhopper (Mascrosteles fascifrons), boll weevil (Anthonomus grandis), two- spotted spider mite (Tetranychus urticae), fall armyworm (Spodoptera frugiperd ⁇ ), black bean aphid ⁇ Aphis fabae), tobacco budworm (Heliothis virescens), rice water weevil (Lissorhoptnis oryzophilus), rice leaf beetle ⁇ Oulema oryzae), wbitebacked planthopper ⁇ Sogatellafurcifera), green leafhopper ⁇ Nephotettixcincticeps), brown planthopper ⁇ Nilaparvata lugens), small brown planthopper ⁇ Laodelphax striatellus), rice stem borer ⁇ Chilo suppressalis), rice leafroller ⁇ Cnaphalocroc
  • Compounds of this invention cai also be mixed with one or more other insecticides, fungicides, nematocides, bactericides, acaricides, semiochemicals, repellants, attractants, pheromones, feeding stimulants or other biologically active compounds to form a multi-component pesticide giving an even broader spectrum of agricultural protection.
  • insecticides such as avermectinB, monocrotophos, carbofuran, tetrachlorvinphos, malathion, parathio — methyl, methomyl, chlordimeform, diazinon, deltamethrin, oxamyl, fenvalerate, esfenvalerate, permethrin, profenofos, sulprofos, triflumuron, diflubenzuron, methoprene, buprofezin, thiodicarb, acephate, azinphosmethyl, chlorpyrifos, dimethoate, fipronil, flufenprox, fonophos, isofenphos, methidathion, methamidophos, phosmet, phosphamidon, phosalone, pirimicarb, phorate, tefbufos
  • Arthropod pests are controlled and protection of agronomic crops, animal and human health is achieved by applying one or more of the compounds of this invention, in an effective amount, to the environment of the pests including the agronomic and/or nonagronomic locus'of infestation, to the area to be protected, or directly on the pests to be controlled.
  • a preferred method of application is by spraying.
  • granular formulations of these compounds can be applied to the plant foliage or the soil.
  • Other methods of application include direct and residual sprays, aerial sprays, systemic uptake, baits, eartags, boluses, foggers, fumigants, aerosols, and many others.
  • the compounds can be incorporated into baits that are consumed by the arthropods or in devices such as traps and the like.
  • the compounds of this invention can be applied in their pure state, but most often application will be of a formulation comprising one or more compounds with suitable carriers, diluents, and surfactants and possibly in combination with a foo ⁇ Tdepending on the contemplated end use.
  • a preferred method of application involves spraying a water dispersion or refined oil solution of the compounds. Combinations with spray oils, spray oil concentrations, spreader stickers, adjuvants, and synergists and other solvents such as piperonyl butoxide often enhance compound efficacy.
  • the rate of application required for effective control will depend on such factors as the species of arthropod to be controlled, the pest's life cycle, life stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, and the like. Under normal circumstances, application rates of about 0.01 to 2 kg of active ingredient per hectare are sufficient to control pests in agronomic ecosystems, but as little as
  • TEST A Fall Armvworm Test units each consisting of a H.I.S. (high impact sytrene) tray with 16 cells were prepared. In 12 of the cells is placed wet filter paper and approximately 8 cm 2 of lima leaf, in the other 4 cells is a 0.5 cm layer of wheat germ diet. Fifteen to twenty third instar larvae of fall armyworm (Spodoptera frugiperda) were placed in a 8 ounce (230 mL) plastic cup. Solutions of each of the test compounds in 75/25 acetone/distilled water solvent were sprayed into the tray and cup.
  • H.I.S. high impact sytrene
  • Spraying was accomplished by passing the tray and cup, on a conveyor belt, directly beneath a flat fan hydraulic nozzle which discharged the spray at a rate of 0.5 pounds of active ingredient per acre (about 0.55 kg ha) at 30 psi (207 kPa).
  • the insects were transferred into the tray (one insect per cell).
  • the trays were covered and held at 27°C and 50% relative humidity for 48 h after which time readings were taken on the 12 cells with lima leaves. The 4 remaining cells were read at 7 days for a delayed toxicity reading. Of the compounds tested, the following gave mortality levels of 80% or higher: 24.
  • Units consisting of an 8-ounce (230 mL) plastic cup containing 1 one-inch square of a soybean-wheatgerm diet were prepared.
  • the test units were sprayed as described in TEST A with individual solutions of the test compounds. After the spray on the cups had dried, five second-instar larvae of the southern com rootworm ⁇ Diabrotica undecimpunctata howardi) were placed into each cup. The cups were then covered and held at 27°C and 50% relative humidity for 48 h, after which time mortality readings were taken.
  • TEST C Boll Weevil Five adult boll weevils ⁇ Anthonomus grandis) were placed into each of a series of 9-ounce (260 mL) cups. The test units were sprayed as described in TEST A with individual solutions of the below-listed compounds. Each cup was then covered with a vented lid and held at 27°C. and 50% relative humidity for 48 h, after which time mortality readings were taken. Of the compounds tested, the following gave mortality levels of 80% or higher: 11, 13, 22, 24, 25, 32, 36, 38, 41, 43*, 45*.
  • Test units were prepared from a series of 12-ounce (350 mL) cups, each containing oat ⁇ Avena sativa) seedlings in a 1-inch (2.5 cm) layer of sterilized soil and a 1/2 inch layer of sand.
  • the test units were sprayed as described in TEST A with individual solutions of the compounds. After the oats had dried from the spraying, between 10 and 15 adult aster leafhoppers ⁇ Mascrosteles fascifrons) were aspirated into each of the cups covered and vented lids.
  • the cups were held at 27°C and 50% relative humidity for 48 h, after which time mortality readings were taken. Of the compounds tested, the following gave mortality levels of 80% or higher: 1, 2, 3, 4, 7, 10, 21*, 22, 24, 25, 29*, 30, 31*, 32, 33, 36, 37, 38*, 40, 42, 43*, 44, 45*.
  • Onejnch squares (2.54 cm) of kidney bean leaves that had been infested on the undersides with 25 to 30 adult mites ⁇ Tetranychus urticae) were sprayed with their undersides facing up on a hydraulic sprayer with a solution of the test compound (acetone/distilled water 75/25 solvent). Spraying was accomplished by passing the leaves, on a conveyer belt, directly beneath a flat fan hydraulic nozzle which discharged the spray at a rate of 0.5 pounds of active ingredient per acre (about 0.55 kg/ha) at 30 psi (207 kPa).
  • the leaf squares were then placed underside-up on a square of wet cotton in a petri dish and the perimeter of the leaf square was tamped down onto the cotton with forceps so that the mites cannot escape onto the untreated leaf surface.
  • the test units were held at 27°C and 50% relative humidity for 48 h, after which time mortality readings were taken. Of the compounds tested, the following resulted in greater than or equal to 80% mortality: 4, 22, 24, 25, 36, 38*, 41, 3*.
  • the turntable completes 7.5 rotations during the 45 second spray interval.
  • treated cups are held in a vented enclosure to dry for about 2 h. After drying, the cups are placed into conical shaped test units and the surface of the soil covered with 2 to 3 mm of quartz sand.
  • Eight to ten 3rd-instar nymphs of the green leafhopper ⁇ Nephotettix cincticeps) are transferred into the test units using an aspirator.
  • the test units are held at 27°C and 65% relative humidity- Counts of the number of live and dead nymphs are taken at 24 and 48 h post-infestation. Insects which cannot walk are classified as dead. Of the compounds tested, the following gave mortality levels of 80% or higher at 48 h at 100 ppm: 2, 3, 4, 5, 7, 9, 11, 12, 13, 17, 21, 22, 24, 25.
  • the turntable completes 7.5 rotations during the 45 second spray interval.
  • treated cups are held in a vented enclosure to dry for about 2 h. After drying, the cups are placed into conical shaped test units and die surface of the soil covered with 2 to 3 mm of quartz sand.
  • Eight to ten 3rd-instar nymphs of the brown planthopper ⁇ Nilaparvata lugens) are transferred into the test units using an aspirator.
  • the test units are held at 27°C and 65% relative humidity, counts of the number of live and dead nymphs are taken at 24 and 48 h post-infestation. Insects which cannot walk are classified as dead. Of the compounds tested, the following gave mortality levels of 80% or higher at 48 h at 100 ppm: 2, 3, 4, 5, 7, 8, 11, 12, 13, 17, 21, 22, 23, 24, 25, 26.
  • the test chemical is added directly into 10 mL of distilled water and dissolved completely.
  • This chemical solution is poured into a conical shaped test unit.
  • Three rice seedlings are then positioned in the unit by a notched sponge disk.
  • the sponge disk allows complete immersion of the seedling root systems in the chemical solution, while the aerial portion of the plant is isolated above the solution.
  • the sponge also prevents the test nymphs from accidentally contacting the test solution.
  • the rice seedlings are allowed to absorb the chemical from the solution for 24 h in a growth chamber held at 27°C and 65% relative humidity.
  • the test chemical is added directly into 10 mL of distilled water and dissolved completely.
  • This chemical solution is poured into a conical shaped test unit.
  • Three rice seedlings are then positioned in the unit by a notched sponge disk.
  • the sponge disk allows complete immersion of the seedling root systems in the chemical solution, while the aerial portion of the plant is isolated above the solution.
  • the sponge also prevents the test nymphs from, accidentally contacting the test solution.
  • the rice seedlings are allowed to absorb the chemical from the solution for 24 h in a growth chamber held at 27°C and 65% relative humidity.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
EP93905036A 1992-04-13 1993-02-04 Arthropodicidal pyrazole sulfonates Withdrawn EP0636121A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US867843 1986-05-27
US86784392A 1992-04-13 1992-04-13
PCT/US1993/001271 WO1993021160A1 (en) 1992-04-13 1993-02-04 Arthropodicidal pyrazole sulfonates

Publications (1)

Publication Number Publication Date
EP0636121A1 true EP0636121A1 (en) 1995-02-01

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ID=25350571

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Application Number Title Priority Date Filing Date
EP93905036A Withdrawn EP0636121A1 (en) 1992-04-13 1993-02-04 Arthropodicidal pyrazole sulfonates

Country Status (6)

Country Link
EP (1) EP0636121A1 (enrdf_load_stackoverflow)
JP (1) JPH07508265A (enrdf_load_stackoverflow)
CN (1) CN1078233A (enrdf_load_stackoverflow)
AU (1) AU3618293A (enrdf_load_stackoverflow)
TW (1) TW227984B (enrdf_load_stackoverflow)
WO (1) WO1993021160A1 (enrdf_load_stackoverflow)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6506784B1 (en) 1999-07-01 2003-01-14 3-Dimensional Pharmaceuticals, Inc. Use of 1,3-substituted pyrazol-5-yl sulfonates as pesticides
US6409988B1 (en) 1999-07-01 2002-06-25 3-Dimensional Pharmaceuticals, Inc. Radiolabeled 1-aryl pyrazoles, the synthesis thereof and the use thereof as pest GABA receptor ligands
AU6116800A (en) 1999-07-22 2001-02-13 3-Dimensional Pharmaceuticals, Inc. 1-aryl-3-thioalkyl pyrazoles, the synthesis thereof and the use thereof as insecticides
US6472416B1 (en) 1999-08-27 2002-10-29 Abbott Laboratories Sulfonylphenylpyrazole compounds useful as COX-2 inhibitors
WO2001025241A2 (en) 1999-10-06 2001-04-12 3-Dimensional Pharmaceuticals, Inc. Fused 1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazoles, the synthesis thereof and the use thereof as pesticides

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB629482A (en) * 1946-03-27 1949-09-21 Du Pont Improvements in or relating to the production of heterocyclic nitrogen compounds
GB631269A (en) * 1946-05-03 1949-10-31 Du Pont Improvements in or relating to pyrazole compounds
DE3228340A1 (de) * 1982-07-29 1984-02-09 Bayer Ag, 5090 Leverkusen Phosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel
US4652574A (en) * 1984-11-14 1987-03-24 Nippon Kayaku Kabushiki Kaisha Certain mono-, di- or tri-substituted pyridyl esters of alkane sulfonic acids having insecticidal, acaricidal and nematocidal properties
US4791127A (en) * 1985-10-07 1988-12-13 Nippon Kayaku Kabushiki Kaisha Alkanesulfonate derivatives and their use as insecticides, acaricides or nematicides
EP0245944A3 (en) * 1986-05-13 1988-10-12 Nippon Kayaku Kabushiki Kaisha Alkanesulfonate derivatives and their use as insecticides, acaricides or nematicides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9321160A1 *

Also Published As

Publication number Publication date
TW227984B (enrdf_load_stackoverflow) 1994-08-11
AU3618293A (en) 1993-11-18
CN1078233A (zh) 1993-11-10
WO1993021160A1 (en) 1993-10-28
JPH07508265A (ja) 1995-09-14

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